Ringing in the New Year in Puerto Rico

We are finally getting back to our regular life after the holidays. We spent 4 days in Dallas to visit family, and then 3 days in Puerto Rico over Christmas.

Ringing in the New Year in Puerto Rico
Photo by Ana Toledo / Unsplash

Sorry no pics on this post. They got nuked after I moved – such is war. When I have time I'll try to come back and reconstruct.

We are finally getting back to our regular life after the holidays.  We spent 4 days in Dallas to visit family, and then 3 days in Puerto Rico over Christmas.  

With 2 kids. Crazy? Maybe. Too short, for sure. But it was all the time my husband could take away from his clients.

While I wish we could have visited longer, a few days was all it took for me to realize how great Puerto Rico really is — and how I can’t wait to go back. (Going back in March… more on that below.)

Our 10-year-old daughter, Kate, is a great traveler. So easy and amicable. Our 3-year-old, Ollie, on the other hand… he’s not so easy.

See those Spiderman headphones in the photo above? I got those for him for Christmas. He smashed them to bits during the first plane ride. Sigh.

As difficult as Ollie is, I have to admit, it is fun traveling with him. On this trip, he really got into suitcase surfing. He’s actually too big for an umbrella stroller, so we don’t bother bringing one anymore. But no worries… whenever Ollie got tired of walking through airports, he just caught a ride on someone’s suitcase.

It occurred to me on this trip that Kate is a great traveler because I traveled with her so much. She has been flying since she was 4 months old. I remember her at 2 years old, full of energy, wearing her princess dresses and plastic Disney high heels, traipsing through the airports when we had to change planes… she never slept, but never complained or whined. She was a soldier. A soldier in princess heels.

We were greeted at the airport by our friends who live in Puerto Rico half the year (Acts 20/22 — tax shelter) and their little puppy, Monkey.


So… ugh… I completely screwed up and ruined our hotel reservations. I thought I had booked them on miles, but I had never used this specific card before to book… and… well, it never got booked.

As a result, we arrived in Puerto Rico with no hotel room. And no vacancies. On the night before New Year’s Eve. My husband was not very happy with me. It was after 11 pm and everyone was exhausted.

Of course, Ollie was not tired at all. You know how some kids just get more energy when they are overtired? That’s our Ollie.

Anyway, we found a backup hotel, which was nowhere near as nice (I had booked a suite on points at the place we didn’t get into). Nonetheless, the other place was perfectly fine and we were grateful that they had potato chips and soda and cava (Spanish champagne) and ice cream in the shop by the front desk. When we finally got up to our room after midnight, we sat around eating chips and drinking cava and processing the stresses of day. It was good to finally relax (and EAT), and good to laugh.

We slept late the next day, and then headed over to the hotel we were supposed to stay at to meet our friends for the buffet brunch.

I had some paella, bacon, and fruit.

And iced coffee and more cava. Hey, it’s vacation! And by the time we got to brunch, it was the afternoon.

After brunch, Seth and Kate stayed at the hotel so Seth could do business meetings.

Ollie and I went with our friend to her condo to help her take some of their luggage over.

They are about 90% done with the renovation. It’s a penthouse apartment in downtown San Juan, with a rooftop pool.

With the Act 20/22 tax incentives, our friends are saving a lot. So they could afford to buy a second home, this condo, in Puerto Rico. If they live in Puerto Rico 6 months per year, they only pay 4% taxes.

Here’s their view from the rooftop pool, which is still under construction…

After that, we headed over to the local liquor store to pick up a few cases of Champagne for that evening’s New Year’s Eve party.

Ollie had fun shopping with us (Ollie has fun everywhere we go).


Seth went out to attend the New Year’s Eve party, which was full of all of his business colleagues… the kids and I were happy to stay home at the hotel and snuggle and play games on tablets and watch the ball drop.

The next morning, we moved from our backup hotel to the Condado Vanderbilt, where we had originally planned to stay.

We ordered tacos, nachos, and French fries, and ate outside overlooking the ocean.

Seth and I started in on the margs. This is a speciality basil margarita.

Thank goodness there was wifi. Plus, Puerto Rico is domestic — there are no texting or phone charges. Just like being in the USA — only you’re in the Caribbean.

After lunch, Ollie and I swam in the pool and Kate and Ollie played in the sand.


We had to check in to our room that day… but couldn’t get in until around 5 or 6 pm. Because it was New Year’s Day, there were a lot of late checkouts… and our room was being cleaned.

When we finally got word that our room was ready, it was getting dark outside and the kids were tired and hungry.

The hotel sent us complimentary churros, ice cream and a glass of wine.

And then they sent me a whole bottle of cava to make up for the wait. And they gave us 50% off our room charge for our first night. Needless to say, that more than made up for the wait to get in the room.

The Condado Vanderbilt is a beautiful hotel. The suites are very spacious and comfortable.

We stayed in a one-bedroom suite with a king size bed in the bedroom and a fold out couch for Kate.

Ollie slept in a crib in the living room area.

The dining area was large and comfortable. We ordered room service both nights for dinner and the food was delicious.

I had to call for help to figure out how to use this coffee maker. Finally figured it out… and the coffee was decent. Not great, but good enough.

At the hotel we stayed in the two nights prior, they had no coffee in the room. I had to take the elevator up to the rooftop pool to order cappuccino. Poor me, eh?

I especially liked the fact that the suite had an ice maker…

You have to pay for the liquor, but all the sodas and tonic waters were complimentary. So we made rum and cokes. The chips and candy bars were complimentary, too, which the kids liked.

Hands down, the best part of the suite was the oceanfront sun deck.

It was giant. Probably bigger than the back yard in our last house.

The next day (our third and final day in Puerto Rico — I know, way too short!), we headed over with our friend (who owns the condo), to their country home, about a 15-minute drive from their condo in San Juan, to help her pick up some things.

The condo didn’t have much damage from the hurricane (just a few windows blown out), but the country home, which they are also in the process of renovating, had some water damage.

At the country house, all the power was still out, so they had had to halt all construction.

They are putting in two pools — one outdoors and one indoors (Ollie is standing in front of the indoor pool).

It’s a huge house, about 8,000 square feet — on I think what she said was an acre. And they have all kinds of fruit trees and wildlife.

The next day, we got on a plane back to Los Angeles. Three short lovely days in Puerto Rico. We’re going back in March for the next CoinAgenda conference and we’ll be looking for a place to rent, with a plan to move there for the summer in May to take part in the Act 20/22 incentives.

Ollie is excited to learn Spanish. He can already say “Hola, como estas?” “Muchas gracias” and “Adios, amigo”. Kate, the animal lover, is looking forward to seeing all the wildlife on the island.

More posts about Puerto Rico to come!